Breaking into a house to watch a woman sleep (more than once) would be more of a red flag to me than a guy who got into a bar fight or was arrested for drunk driving. It's just... creepy. Combine it with his surface likability and penchant for habitual lying and you're part of the way to a zero-empathy diagnosis and a possibly serious personality disorder.
I just hope the guy doesn't do something violent once he gets out of prison, because some of the warning signs are there. That's why I think he's spent so much time in prison. These kinds of actions can be a sign of someone who has the potential for seriously sick and violent crimes.
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